Author: tianli

Adding some certain compound to certain chemical reactions, such as: 603-62-3, name is 3-Nitrophthalimide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 603-62-3. 603-62-3

Thiosalicylic acid (15.4 g, 0.1 mol) in NaOH aqueous solution (200 mL, 1 mol/L) was warmed until the solid dissolved, and then continually warmed to remove water. Ethanol was added into the sticky mixture, and then the white precipitates were collected by filtration, washed with ethanol, and dried in vacuo to obtain sodium thiosalicylate (f). A mixture of f (18.215 g, 0.1034 mol), 3-nitrophthalimide (15.892 g, 0.0827 mol), and DMF (200 mL) was stirred at 80 C for 8 h. A HCl solution (200 mL, 2 mol/L) was added. The precipitate was filtered, washed with water, dried in vacuo, and then recrystallized from dioxane to give a yellow powder. Yield: 95.4%. 1H NMR (300 MHz, DMSO-d6): delta 7.29-7.31 (m, 2H), 7.47 (m, 2H), 7.66 (m, 2H), 7.86 (m, 1H). Anal. Calcd. for C15H9NO4S: C, 60.19; H, 3.03; N, 4.68; S, 10.71; Found: C, 59.48; H, 3.20; N, 4.54; S, 10.51.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Nitrophthalimide.

Reference:
Article; He, Ming-Hui; Xu, Rui-Xin; Chen, Guang-Xue; Zeng, Zhao-Hua; Yang, Jian-Wen; Chinese Chemical Letters; vol. 25; 11; (2014); p. 1445 – 1448;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2058-74-4, name is 1-Methylisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 2058-74-4

General procedure: A solution of N-methylisatin (81 mg, 0.5 mmol), phenylacethylene (77 mg, 0.75 mmol), CuI (19 mg, 0.1 mmol), and Cs2CO3 (245 mg, 0.75 mmol) in CH3CN (1.0 mL) was stirred at room temperature for 18 h. After aqueous extractive work up and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 81 mg (61%). Other compounds were prepared similarly, and the spectroscopic data of unknown compounds 1b, 1d, and 1e are as follows.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roh, Hwa Jung; Lim, Jin Woo; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 57; 38; (2016); p. 4280 – 4283;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 104618-32-8 name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 104618-32-8

EXAMPLE 14 3-Amino-6-n-butyloxy-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (1.12 g) with 4-n-butyloxyphenyl hydrazine hydrochloride (1.00 g) and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.47 g), mp 227-229 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6326-79-0, 6326-79-0

To a solution of 6-bromoindoline-2,3-dione (0.504 g,2.23 mmol)in acetonitrile (11 mL)was added K2C03 (1.23 g,8.92 mmol)then iodomethane (0.278 mL,4.46 mmol). The reactionmixture was heated at 60 oc for 1.5 h. After cooling to room temperature,water (30 mL)wasadded and the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine (30 mL),dried over anhydrous Na2S04 and then concentrated in underreduced pressure to give the title compound (0.506 g,95%)that required no further purification.1HNMR(400MHz,CDCl3)87.46(dd,J=7.9,l.OHz,1H),7.32-7.28(m,1H),7.08(d,J=1.5 Hz,1H),3.25 (d,J = 0.6 Hz,3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2436-29-5

Step 3. 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4- yI)methyl)(methyl)amino)propyl)isoindoline-l,3-dioneTo a stirred solution of 9-((3aR,4R,6R,6aR)-2,2-dimethyl-6- ((methylamino)methyl)tetrahydrofuro[3,4-d][ l ,3]dioxol-4-yl)-9H-purin-6-amine (1.6 g, 5.0 mmol) and 3-(l,3-dioxoisoindolin-2-yl)propanal (2.0 g, 9.8 mmol) in 50 mL DCE was added NaBH(OAc)3 (3.18 g, 15.0 mmol). Then the mixture was stirred at rt overnight. Saturated NaHC03 aqueous solution was added to quench the reaction and the mixture was extracted with DCM (20 mL x 4). The organic phase was concentrated and the residue was purified by SGC (CH3OH : DCM = 1 : 100) to afford the title compound (2.47 g, yield: 94%) as white solid. NMR (500 MHz, MeOD): delta 8.26 (s, 1H), 8.21 (s, 1H), 7.77-7.84 (m, 4H), 6.15 (d, J = 2.5 Hz, 1H), 5.45-5.47 (m, 1H), 5.01-5.03 (m, 1H), 4.34-4.35 (m, 2H), 363-3.69 (m, 2H), 2.70-2.72 (m, 2H), 2.46-2.50 (m, 2H), 2.27 (s, 3H), 1.74-1.78 (m, 2H), 1.37 (s, 3H), 1.24 (s, 3H) ppm. MS (ESI): m/z 508.7 [M+l]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2436-29-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

181140-34-1, A common compound: 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To DMF solution (20 ml) of N-(2(R), 3-epoxypropyl)phthalimide 2.51 g (12.4 mmol), sodium azide 1.61 g (24.7 mmol) and ammonium chloride 0.79 g (14.9 mmol) were added, and stirred at 80 C. for 3 hours. The reaction mixture was allowed to stand at room temperature overnight. Benzene (50 ml) and distilled water (50 ml) were poured into the reaction mixture and organic layer was washed with water, brine sequentially, dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and filtrate was evaporated in vacuo. Further purification by silica gel chromatography gave 1.96 g of desired product. The NMR, FAB-MS spectra were consistent with the desired title intermediate. 1H-NMR(270 MHz,CDCl3)delta: 3.03(1H,d), 3.36-3.49(2H,m,), 3.85(2H,d), 4.05-4.13(1H,m), 7.73-7.78(2H,m), 7.84-7.90(1H,m). FAB-MS: m/z 247(M+H)+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Molecular Research Institute; US2006/14701; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 324-03-8 as follows.

To a 250 mL round-bottom flask was added 6-fluoro-2,3-dihydro-lH-indole-2,3-dione (8 g, 48.45 mmol, 1.0 equiv.), iodomethane (15.1 g, 106.38 mmol, 2.2 equiv.), potassium carbonate (26.7 g, 193.18 mmol, 4.0 equiv.), and CH3CN ( 150 mL). The resulting mixture was stirred overnight at 60 C. The reaction was quenched with water. The resulting solution was extracted with ethyl acetate (100 mL x 3); and the combined organic layers were washed with brine (50 mL x 2), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified via silica gel column chromatography eluting with ethyl acetate/petroleum ether (20%-40%) to give 6-fluoro-l-methyl-2,3-dihydro-lH-indole-2,3-dione 30b (7 g, 81%) as a red solid.

According to the analysis of related databases, 6-Fluoroindoline-2,3-dione, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 118289-55-7

10. Preparation of ziprasidone in toluene In a 250 ml three necked flask was charged BITP HCl (5g), Na2C03 (6. 5g), CEI (5g), NaI (1. 5g) and toluene (30ml) ; the mixture was heated at reflux for 22.5 hours. After cooling to the room temperature the reaction product was filtrated, washed with methanol and triturated in water. After drying the product weights 7.27g (yield 86%, purity by HPLC 98.3%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 118289-55-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

222036-66-0, The chemical industry reduces the impact on the environment during synthesis 222036-66-0, name is 5-Aminoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

To a solution of 5-aminoisoindolin-1-one (2.96 g, 20 mmol) in chloroform (50 mL) was added N-chlorosuccinimide (2.67 g, 20 mmol), and stirred under reflux for 2 hours. The resulting mixture was evaporated, concerntrated and then purified by silica gel column chromatography to give 4-chloro-5-aminoisoindolin-1-one (2.58 g). Yield: 70percent. MS m/z[ESI]: 183.0[M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Aminoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 20870-78-4

To a stirred solution of 5-bromoindolin-2-one (LIV, 7.25 g, 34.36 mmol) in tetrahydrofuran (70 mL) under nitrogen atmosphere, was added sodium hydride (5.9 g, 137.0 mmol) portion-wise at 0 C. After addition of sodium hydride, the reaction was stirred at room temperature for 30 min, then cooledto 0 C. methyl iodide (8.5 mL, 137.0 mmol) was added, and then allowed to stir at room temperature for 2h. The reaction mass was cooled to 0 C and carefully quenched with ice-water. Then the reaction mixture was diluted with water (150 mL) and ethylacetate (150 mL). The organic layer was separated, washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford the titled product as brown colour solid (LV, 7.4 g, 85%). LC-MS m/z calcd for CnHi2BrNO, 253.0; found 254.0 [M+H]+.

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; RAJAGOPAL, Sridharan; HALLUR, Mahanandeesha S.; DEWANG, Purushottam; MURUGAN, Kannan; KUMAR C.H., Durga Prasanna; IYER, Pravin; MULAKALA, Chandrika; SIVANANDHAN, Dhanalakshmi; NAIR, Sreekala; ZAINUDDIN, Mohd.; TANTRY, Subramanyam Janardhan; GAJENDRAN, Chandru; RAJAGOPAL, Sriram; (334 pag.)WO2017/195216; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem